
Holiday houses in Cerchiaia
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Top-rated holiday rentals in Cerchiaia
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Casa al Gianni - The Simignano Barn
Transformed from a historic barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living area, and a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit and an outdoor kitchen. Ideal for those looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, with relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this little slice of paradise!

The little house
We open the doors of our house in the Siena countryside, 7 minutes by bus from the centre (stop 2 minutes away). A small, functional nest, designed to make you feel at home, ideal for couples or singles. It offers a double bedroom and a small bedroom with a sofa bed: to ensure total comfort, we recommend it for 2/3 guests, but it can accommodate up to 4. The kitchen is spacious and equipped; the bathroom, although small, is complete with everything. Free parking in front of the house, no limited traffic zone.

Palazzo Monaci - Pool in the Crete Senesi
Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Villa di Geggiano – Guesthouse
PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

La Mattonaia, free private parking
Just outside the city walls, this bright apartment with a garden is served by city buses to the historic center, stopping right outside the gate. Strada Massetana Romana is home to a wide range of shops: supermarkets, a pharmacy, bars, a bank, clothing stores, and more. The apartment comprises a spacious double bedroom, a bathroom with shower, a fully equipped kitchen, and a spacious living room. Guests have access to convenient free parking within the fenced property with an automatic gate.

Apartment in historic Villa in Siena_"Il Campo"
The apartment "Il Campo" is part of "Villa il Borghetto - Apartments". Villa il Borghetto offers apartments in Siena in a historic Villa, with the guarantee of an authentic hospitality, thanks to the family management of the "landlords". Villa il Borghetto has been designed to accommodate families wishing to experience Siena as a local, offering a convenient location to visit Siena without giving up the view of the Typical Tuscany rolling hills and the convenience of a free private parking.

Podere Piazza house with panoramic view
Podere Piazza ist ein Landgut, hat seinen Ursprung im 15. Jahrhundert, das Ferienhaus wurde Anfang 17. Jahrhundert erbaut. Podere Piazza war der Wohnsitz von Alessandro Cervini degli Spannocchi, der am 29 Mai 1747 zum Erzbischof von Siena ernannt wurde, er war ein Nobile di Montepulciano und Patrizier von Siena. Die Gebäude von Podere Piazza tragen noch heute sein Wappen. Somit erklärt sich auch unser Kirchlein, am Straßenabzweig, davor rechts zur Pinienallee und links in die Einfahrt.

Luxury penthouse with a view of Piazza del Campo
There are many houses in Siena. But very few can say they are here. Overlooking the city's most iconic square, this penthouse offers a rare experience: waking up with the golden light that caresses the Palazzo Pubblico and falling asleep above one of the most beautiful places in the world. The location is simply one of a kind. Just outside the door, you are immersed in history, among restaurants, wines and timeless atmospheres.

L'Apparita del Peruzzi | Villa | Private pool & air conditioning
A Renaissance villa attributed to Baldassarre Peruzzi, set in a private panoramic park located in the countryside near Siena (just 5,8 km from Piazza del Campo). Offered for exclusive use, the property features six bedrooms, a secluded private pool (May–September), and gardens designed by famous architect Pietro Porcinai, providing space, privacy and an authentic Tuscan experience for families and groups.

"Villa Daisy" overlooking Siena
Wonderful villa with independent entrance inside the "Caggiolo" farm, brought to light with careful and thorough renovation that has kept intact the typical features of a Tuscan farm. Beautiful panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).

The Palazzetto - Granaio (Superior 4+2)
Located inside the ancient residence "IL PALAZZETTO". "Granaio" is a large independent house located in the old grain store of the property, now renovated in a modern annex. The house consists of a large living room-kitchen with a double sofa bed, two large double bedrooms, one of which has a private bathroom with shower. Includes TV, independent heating, air conditioning, private parking, Wi-Fi.

Strategic Apartment
A new renovated apartment, Perfect for who wants to visit siena and the countryside as well ( Chianti, Montalcino ecc). The historic city center reachable by car in 5 minutes. You can park your car at the gas station near the apartment. *** IF YOU DON’T HAVE A CAR, IT WOULD BE VERY INCONVENIENT.
Popular amenities for Cerchiaia holiday rentals
Other great holiday rentals in Cerchiaia

Molino delle Fate

Malamerenda's House in Siena

Elf Hut

Luxury Medieval Tower • Exclusive Chianti Stay

Pool Escape Just Outside Siena

Cipressini 2 - pool and amazing views

Poggiolo

Elegant farmhouse overlooking Pienza
Destinations to explore
- Cathedral of Santa Maria del Fiore
- Lake Trasimeno
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Mugello Circuit
- Cala Violina
- Parco Regionale Della Maremma
- Mercato Centrale
- Uffizi Gallery
- Stazione Santa Maria Novella
- Fortezza da Basso
- Piazza della Repubblica
- Spiagge Bianche
- Parco delle Cascine
- Del Chianti
- Piazzale Michelangelo
- Gulf of Baratti
- Pitti Palace
- Boboli's Garden
- Palazzo Vecchio
- Piazza della Signoria
- Cascate del Mulino





